Henry Flagler, Original Florida Man

On losing your legacy

Florida Man is an Internet meme first popularized in 2013,^[1] referring to an alleged prevalence of people performing irrational or maniacal actions in the U.S. state of Florida.

-Wikipedia

In 1890, Key West was the most populous city in Florida. The port ranked thirteenth busiest in the nation and exported 62 million cigars a year. All of this was happening on an island four miles long and one mile wide. As oil baron Henry Flagler’s Overseas Railroad neared completion in 1912, connecting the so-called Southernmost City to the rest of the country, the fervor took the media and government officials by storm with the promise of easy transport of pineapples, tropical fruits, and vegetables from warmer climates. One representative, once against the project, enthused that Flagler, co-founder of Standard Oil and now much of Florida, was now “the direct cause of providing happy and contented homes for 50,000 people.”

Les Standiford’s Last Train to Paradise (2002) tells us the details. As one newspaper projected:

“Old Key West [will be] shaking off its lethargy… with the spirit of progress and development will be greater than ever.”

As we covered previously, building a railroad across the ocean wasn’t easy. Hurricanes happened. More than 200 people died. But who wouldn’t be optimistic - or at least impressed - after watching a man who just wouldn’t quit, who seemed unable to quit, as he defied the wrath of governments and nature alike to connect the unconnected with the bright spirit of a better future?

After all, Henry Flagler could literally summon land into existence. The Key West terminal for the Overseas Railroad, meant for all the commercial freight traffic, was built on land dredged and molded to purpose for a 1,700-foot pier that spanned 134 feet to allow trains to pull up directly to ocean liners with the purpose of transporting pineapples and promises from Cuba across the United States.

Officially opened in January 21, 1912, the Overseas Railroad’s media nickname changed from Flagler’s Folly to the Eighth Wonder of the World. As one journalist explained, as if Flagler himself had laid each track:

Everything that went into the construction of this work obeyed his will… the Greeks before Troy suffered no greater hardships, no greater heroism.

On his opening day victory ride, Flagler, age eight-two, entered Car 91, the 1886 luxury sleeper car Standiford describes as a “copper-roofed pleasure palace” replete with Victorian wood paneling for the lounge and stateroom, with a copper-lined shower, dining area, and both guest and private quarters, and traveled 220 miles from West Palm Beach to Key West where he was greeted by throngs of people screaming for him as if a hero of legend. As Florida governor Albert Gilchrist described it:

The building of this great oversea ralroad is of nationwide importance, second in importance only to the construction of the Panama Canal.

Did the Overseas Railroad live up to Henry Flagler’s expectations? As he put it in his correspondence:

I thank God that from the summit I can look back over the 25 or 26 years since I became interested in Florida… I can die happy. My dream is fulfilled.

By all appearances, Flagler truly wanted to leave something behind for humankind. This irrational pursuit of his legacy - in the form of a railroad across the ocean in the most hurricane-prone region of the country - clearly shows that he, in addition to founding so many parts of the Florida we know today, also embodied that charmingly insane meme of Florida Man to his core. It is Florida Man, not the railroad, that would become his real legacy.

Even in arriving to Key West on the railroad he had built over the ocean, Flagler seems to know that he is leaving something in a world that is rapidly leaving him. Disembarking to fanfare in Key West at the station he built all the way from nowhere and from nothing, Flagler, suffering from failing eyesight, explained to his companions:

“I can hear the children, but I cannot see them.”

What made Flagler unable to stop? Had he really fulfilled his dream with this railroad? This question haunts the history: If a legacy is doomed to destruction, is it a legacy at all?

Standiford cites reporter Edwin Lefevre’s 1910 interview. As Lefevre writes:

Flagler’s is not only an excessive modesty but a personality so elusive as to be unseizable… He has no intimates.

This gives way to this exchange:

“You don’t seem to care to talk about yourself.”

”I prefer to let what I have done speak for me,” Flagler replied.

“By their works ye shall know them.”

“Yes; that’s it,” Flagler said - as eagerly as he had said anything, according to interviewer.

As eagerly as an elusive personality said anything: in other words, not very. Lefevre pivots to the Florida landscape, recollecting:

All that day I had tried to catch a glimpse of this man’s soul- in vain… and now in the loggia of his palace, looking out to Lake Worth.. I turned… and… I asked him, I fear impatiently:

‘Doesn’t this sky get into your soul? Doesn’t that glow light it… isn’t this the real reason why you do things here?’

Flagler replied:

“Sometimes, at the close of day, when I am fortunate enough to be alone, I come here… I look at the water and at the trees yonder and at the sunset… [and] I often wonder if there is anything in the other world so beautiful as this.”

This exchange reminds us that Flagler, coming from Ohio, had never seen the world past the cold East Coast until Florida. The awe he felt for the land was real and the reader is left wondering if the true reason he couldn’t quit was because he felt the most connected to this new paradise he discovered in his twilight years and he was really already in paradise when he was building the future for this paradise, not anticipating the other one.

Legacy Lost

In Hemingway’s To Have and to Have Not (1937), we visit a desperate Key West after the 1935 Labor Day Hurricane that destroyed the railroad and left more than 200 World War I veterans dead. Hemingway, a Key West resident since 1928, was on the ground in the aftermath, helping look for survivors in the devastation. You can read more of that here.

In To Have and to Have Not, we visit a wealthy grainer broker sleeping alone in his yacht. As Hemingway describes him:

His wife had divorced him ten years before after twenty years of keeping up appearances, and he had never missed her nor had he ever loved her. He had started with her money and she had borne him two male children, both of whom, like their mother, were fools. he had treated her well until the money he had made was double her original capital and then he could afford to take no notice of her. After his money had reached that point he had never been annoyed by her sick headaches, by her complaints, or by her plans. He had ignored them…

Flagler, a former grainbroker, founded Standard Oil, in part, because of his brother-in-law’s money. His wife’s money. After his wife passed, he married her caregiver, Ida Alice Shourds, who eventually became declared insane - which, according to a new 1901 law passed with considerable influence from Flagler - became grounds for divorce in Florida.

What else does Hemingway say about the grainbroker?

He had been admirably endowed for as speculative career because he had possessed extraordinary sexual vitality which gave him the confidence to gamble well; common sense, an excellent mathematical brain, a permanent bit controlled skepticism; a skepticism which was as sensitive to impending disaster as an accurate aneroid barometer to atmospheric pressure; and a value time sense that kept him from trying to hit tops or bottoms. These, coupled with a lack of morals, an ability to make people like him without ever liking or trusting them in return, while at the same time convincing them warmly and heartily of his friendship; not a disinterested friendship; but a friendship so interested in their success that it automatically made them accomplices; and an incapacity for either remorse or pity, had carried him to where was now.

In this description, we might feel less sympathy for Flagler. Most charitably, we might picture him as an engineer whose real paradise came from the work, not the creation and only found meaning in new challenges he interpreted as if divine gifts.

As Lefevre guessed: Flagler built, because his philosophy was that the people would know him by his work. There was no other way to know him.

The full verse of knowing a man by his work is from the Book of Mormon, Moroni 7:5-15, as the angel Moroni explains to prophet Joseph Smith:

For I remember the word of God, which saith by their works ye shall know them; for if their works be good, then they are good also.

For behold, God hath said a man being evil cannot do that which is good; for if he offereth a gift, or prayeth unto God, except he shall do it with real intent it profiteth him nothing.

For behold, it is not counted unto him for righteousness.

For behold, if a man being evil giveth a gift, he doeth it grudgingly; wherefore it is counted unto him the same as if he had retained the gift; wherefore he is counted evil before God.

A work of good is known as good, in this verse, when it is done without expectation. Hemingway clearly didn’t fall for the worship of Henry Flagler and offered a comeuppance in razor-sharp caricature at the height of the novel’s resolution.

This interpretation, however, hinges on a clear sense of self from the grain broker in the book. Flagler, in most records, shows the emotional capacity of Sam Bankman-Friedman: his feelings for people or projects are organized by the same random number generator the greedily well-intentioned call Effective Altruism.

Flagler created works big enough, at scale, to prove virtue as calculation, invention as blessing, and distribution as forgiveness without considering whether numbers are as real as gravity or concrete stands as long as memory.

He built as if building was a blessing.

Who’s to say? Not even Moroni tells us, as he ends the verse:

Wherefore, take heed, my beloved brethren, that ye do not judge that which is evil to be of God, or that which is good and of God to be of the devil.

For behold, my brethren, it is given unto you to judge, that ye may know good from evil; and the way to judge is as plain, that ye may know with a perfect knowledge, as the daylight is from the dark night.

At the end of Last Train to Paradise, the reader is left to judge the success of the Overseas Railroad, and by extension, Henry Flager himself. It was destroyed within a few decades. Did it at least meet market expectations? No. Standiford makes it clearer those were destroyed from the start. The railroad was a commercial failure and lasted barely more than twenty years.

So we have to zoom out to get Flagler’s real legacy in focus: he was the original Florida Man. In the stubborn surety of his irrational pursuits, he inspired and created a state and a people and a spirit all around it. His recklessness and incomprehensible emotions, maybe, were the fuel for his genius and the destiny that led him there. Let’s say it again: the Overseas Railroad shows us that Henry Flager was the original Florida Man.

What did God think? Well, given that the railroad was obliterated, we might think he didn’t care for Flagler. After all, he died alone in his mansion 1913, just one year after the railroad was completed. The mansion was even on a part of Long Island Sound called Satan’s Toe. Also, he died trying to go to the bathroom.

At 83, Henry Flagler attempted to turn on a lightswitch for the toilet but accidentally triggered a pneumatic device that opened the door automatically. The door smacked Flagler straight off a staircase.

As Standiford stressfully tries to describe it, the door’s impact on Flagler’s body was:

Like a tidal surge blasting through ha channel in the upper keys, the rush of the heavy door is an implacable force.

This is easier to picture when you don’t call the thing a “pneumatic device” but a door closer. At the turn of the nineteenth-century, these door closers were all the rage. On Wikipedia, which offers definitions for “seven configurations of interior door-closer,” we can find menacing pictures of these murder devices.

Floor spring for pneumatic door opening device (Source: Wikipedia)

Antique door opener, likely 19th century (Source: Wikipedia)

Even in his eighties, Flagler wanted to adopt the latest marvels of engineering. If Hemingway’s grain broker is killed by appetite, Flagler died an engineer’s death in trying to do something human, like go to the bathroom, but, like every time before, the miracle machine of his mind sent him somewhere else. This time, for good.

The most tempting response to the ultimate doom of the railroad is an 1818 sonnet from Percey Shelly: Ozymandias.

I met a traveller from an antique land
Who said: Two vast and trunkless legs of stone
Stand in the desart.^[d] Near them, on the sand,
Half sunk, a shadfttered visage lies, whose frown,
And wrinkled lip, and sneer of cold command,
Tell that its sculptor well those passions read
Which yet survive, stamped on these lifeless things,
The hand that mocked them and the heart that fed:
And on the pedestal these words appear:
"My name is Ozymandias, king of kings:
Look on my works, ye Mighty, and despair!"
Nothing beside remains. Round the decay
Of that colossal wreck, boundless and bare
The lone and level sands stretch far away.

The forgotten king, the empire turned to dust, shows that all power is temporary, all sense of grandeur a delusion. Yet what if legacy is not material, but a ripple in the sea of the spirit we all share?

In Shelley’s poem, the real legacy of Ozymandias is not the empire dissolved to sand but the fragment of the dream that inspires the feelings and thoughts that inspire the conversation and the poem.

It might not matter for Henry Flagler that the Overseas Railroad is now best remembered in state parks and chunks of railroad sitting alongside the highway to Key West. Maybe it’s enough that someone looks out the window to see what the original Florida Man tried to do not because it was logical but because he couldn’t help himself. It doesn’t even matter that they know Flagler’s name: every legacy, eventually, is a legend that is felt, not named.

Or in this case, building a railroad in the ocean where some of the most dangerous hurricanes in the world form, maybe the legend does have a name: Florida Man.